diff --git a/src/network.cpp b/src/network.cpp
index 887d762..613c234 100644
--- a/src/network.cpp
+++ b/src/network.cpp
@@ -16,6 +16,7 @@
 
 #include "socket.h"
 
+#include <atomic>
 #include <mutex>
 #include <string>
 #include <thread>
@@ -24,7 +25,7 @@ namespace {
 
 class Impl : public dap::net::Server {
  public:
-  Impl() {}
+  Impl() : stopped{true} {}
 
   ~Impl() { stop(); }
 
@@ -41,17 +42,18 @@ class Impl : public dap::net::Server {
       return false;
     }
 
-    running = true;
+    stopped = false;
     thread = std::thread([=] {
-      do {
+      while (true) {
         if (auto rw = socket->accept()) {
           onConnect(rw);
           continue;
         }
-        if (!isRunning()) {
+        if (!stopped) {
           onError("Failed to accept connection");
         }
-      } while (false);
+        break;
+      };
     });
 
     return true;
@@ -63,23 +65,19 @@ class Impl : public dap::net::Server {
   }
 
  private:
-  bool isRunning() {
-    std::unique_lock<std::mutex> lock(mutex);
-    return running;
-  }
+  bool isRunning() { return !stopped; }
 
   void stopWithLock() {
-    if (running) {
+    if (!stopped.exchange(true)) {
       socket->close();
       thread.join();
-      running = false;
     }
   }
 
   std::mutex mutex;
   std::thread thread;
   std::unique_ptr<dap::Socket> socket;
-  bool running = false;
+  std::atomic<bool> stopped;
   OnError errorHandler;
 };
 
diff --git a/src/network_test.cpp b/src/network_test.cpp
index 8e965f1..57bb0a9 100644
--- a/src/network_test.cpp
+++ b/src/network_test.cpp
@@ -25,6 +25,8 @@
 
 namespace {
 
+constexpr int port = 19021;
+
 bool write(const std::shared_ptr<dap::Writer>& w, const std::string& s) {
   return w->write(s.data(), s.size()) && w->write("\0", 1);
 }
@@ -44,7 +46,6 @@ std::string read(const std::shared_ptr<dap::Reader>& r) {
 }  // anonymous namespace
 
 TEST(Network, ClientServer) {
-  const int port = 19021;
   dap::Chan<bool> done;
   auto server = dap::net::Server::create();
   if (!server->start(
@@ -59,15 +60,51 @@ TEST(Network, ClientServer) {
     return;
   }
 
-  for (int i = 0; i < 10; i++) {
-    if (auto client = dap::net::connect("localhost", port)) {
-      ASSERT_TRUE(write(client, "client to server"));
-      ASSERT_EQ(read(client), "server to client");
-      break;
-    }
+  for (int i = 0; i < 5; i++) {
+    auto client = dap::net::connect("localhost", port);
+    ASSERT_NE(client, nullptr) << "Failed to connect client " << i;
+    ASSERT_TRUE(write(client, "client to server"));
+    ASSERT_EQ(read(client), "server to client");
+    done.take();
     std::this_thread::sleep_for(std::chrono::seconds(1));
   }
 
-  done.take();
+  server.reset();
+}
+
+TEST(Network, ServerRepeatStopAndRestart) {
+  dap::Chan<bool> done;
+  auto onConnect = [&](const std::shared_ptr<dap::ReaderWriter>& rw) {
+    ASSERT_EQ(read(rw), "client to server");
+    ASSERT_TRUE(write(rw, "server to client"));
+    done.put(true);
+  };
+  auto onError = [&](const char* err) { FAIL() << "Server error: " << err; };
+
+  auto server = dap::net::Server::create();
+  if (!server->start(port, onConnect, onError)) {
+    FAIL() << "Couldn't start server";
+    return;
+  }
+
+  server->stop();
+  server->stop();
+  server->stop();
+
+  if (!server->start(port, onConnect, onError)) {
+    FAIL() << "Couldn't restart server";
+    return;
+  }
+
+  auto client = dap::net::connect("localhost", port);
+  ASSERT_NE(client, nullptr) << "Failed to connect";
+  ASSERT_TRUE(write(client, "client to server"));
+  ASSERT_EQ(read(client), "server to client");
+  done.take();
+
+  server->stop();
+  server->stop();
+  server->stop();
+
   server.reset();
 }
diff --git a/src/socket.cpp b/src/socket.cpp
index 998fed9..1211310 100644
--- a/src/socket.cpp
+++ b/src/socket.cpp
@@ -174,7 +174,17 @@ class dap::Socket::Shared : public dap::ReaderWriter {
       if (s != InvalidSocket) {
 #if defined(_WIN32)
         closesocket(s);
+#elif __APPLE__
+        // ::shutdown() *should* be sufficient to unblock ::accept(), but
+        // apparently on macos it can return ENOTCONN and ::accept() continues
+        // to block indefinitely.
+        // Note: There is a race here. Calling ::close() frees the socket ID,
+        // which may be reused before `s` is assigned InvalidSocket.
+        ::shutdown(s, SHUT_RDWR);
+        ::close(s);
 #else
+        // ::shutdown() to unblock ::accept(). We'll actually close the socket
+        // under lock below.
         ::shutdown(s, SHUT_RDWR);
 #endif
       }
@@ -182,7 +192,7 @@ class dap::Socket::Shared : public dap::ReaderWriter {
 
     WLock l(mutex);
     if (s != InvalidSocket) {
-#if !defined(_WIN32)
+#if !defined(_WIN32) && !defined(__APPLE__)
       ::close(s);
 #endif
       s = InvalidSocket;
@@ -240,10 +250,13 @@ std::shared_ptr<ReaderWriter> Socket::accept() const {
   std::shared_ptr<Shared> out;
   if (shared) {
     shared->lock([&](SOCKET socket, const addrinfo*) {
-      if (socket != InvalidSocket) {
+      if (socket != InvalidSocket && !errored(socket)) {
         init();
-        out = std::make_shared<Shared>(::accept(socket, 0, 0));
-        out->setOptions();
+        auto accepted = ::accept(socket, 0, 0);
+        if (accepted != InvalidSocket) {
+          out = std::make_shared<Shared>(accepted);
+          out->setOptions();
+        }
       }
     });
   }